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Spin labelled C-glycoside analogs : derivatives of 1,4-anhydro-4-deoxy-2,3-O-cyclopentylidene-1,4-N-hydroxyimino-DL-erythrofuranose

Authors
Tronchet, Jean M.J.
Balkadjian, Mirna
Zosimo-Landolfo, Guido
Barbalat-Rey, Françoise
Lichtle, Patrick
Ricca, Alessandra
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Published in Journal of Carbohydrate Chemistry. 1995, vol. 14, no. 1, p. 17-34
Abstract A series of 2,3-O-cyclopentylidene C-glycoside analogs in which the furanose ring has been replaced with a N-hydroxypyrrolidine have been prepared. A structural study of these tricyclic compounds and the aminoxyl radicals thereof has been carried out using variable temperature 1H NMR, X-ray diffraction, molecular dynamics and EPR spectroscopy. Both types of compounds, N-hydroxypyrrolidines and pyrrolidine N-oxyls, fundamentally prefer - in solutions- N-endo conformations over the alternate, N-exo forms found by X-ray diffraction studies and computed to be more stable by molecular dynamics.
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Research group Groupe Geoffroy
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TRONCHET, Jean M.J. et al. Spin labelled C-glycoside analogs : derivatives of 1,4-anhydro-4-deoxy-2,3-O-cyclopentylidene-1,4-N-hydroxyimino-DL-erythrofuranose. In: Journal of Carbohydrate Chemistry, 1995, vol. 14, n° 1, p. 17-34. https://archive-ouverte.unige.ch/unige:2844

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Deposited on : 2009-09-21

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